%0 Journal Article
%A Xiao, Sa
%A Chen, Chao
%A Li, Hongyan
%A Lin, Kuaile
%A Zhou, Weicheng
%D 2015
%T A Novel
and Practical Synthesis of Ramelteon
%U https://acs.figshare.com/articles/journal_contribution/A_Novel_and_Practical_Synthesis_of_Ramelteon/2194390
%R 10.1021/op500386g.s001
%2 https://ndownloader.figshare.com/files/3828718
%K ethylamine compound 13
%K Practical Synthesis
%K olefin reduction
%K acid
%K hydrogenation
%K synthesis
%K resolution agent
%K target compound 1
%K cyano reduction
%K nucleophilic reagent
%X An efficient and practical process
for the synthesis of ramelteon 1, a sedative-hypnotic,
is described. Highlights in this synthesis
are the usage of acetonitrile as nucleophilic reagent to add to 4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one 2 and the subsequent hydrogenation which successfully implement four
processes (debromination, dehydration, olefin reduction, and cyano
reduction) into one step to produce the ethylamine compound 13 where dibenzoyl-l-tartaric acid is selected both
as an acid to form the salt in the end of hydrogenation and as the
resolution agent. Then, target compound 1 is easily obtained
from 13 via propionylation. The overall yield in this
novel and concise process is almost twice as much as those in the
known routes, calculated on compound 2.
%I ACS Publications